Patents by Inventor Herbert C. Brown

Herbert C. Brown has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5068432
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: November 26, 1991
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5043479
    Abstract: Novel chemically pure diisopinocampheylhaloboranes of essentially 100% ee, represented by the formula Ipc.sub.2 BX wherein Ipc is isopinocampheyl and X is halo.
    Type: Grant
    Filed: September 1, 1989
    Date of Patent: August 27, 1991
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4978794
    Abstract: 2-Alkenylbis(2-isocaranyl)boranes represented by the formula: ##STR1## wherein R is 2-alkenyl. The compounds undergo asymmetric 2-alkenylboration with a variety of aldehydes and afford the corresponding alcohols in 94-99% ee.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: December 18, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4950791
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: August 21, 1990
    Inventor: Herbert C. Brown
  • Patent number: 4918242
    Abstract: A process for producing the optically pure (+)- or (-)-isomer of a phenyl- or substituted-phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4918246
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4918207
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a pheynl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Co., Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4918229
    Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMBe.sub.2 wherein R is an organo group, R* is a chiral organo group attached to boron, B is boron and Me is methyl.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4895996
    Abstract: Alkenes are prepared by the hydroboration of enamines followed by an elimination reaction to form the alkene. This process has wide applicability and is useful for the stereospecific synthesis of [Z] isomers. It is preferred to use 9-borabicyclo[3.3.1 nonane as the hydroborating agent and to use methanol to catalyze the elimination reaction.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: January 23, 1990
    Assignees: Purdue Research Foundation, The Dow Chemical Company
    Inventors: Christian T. Goralski, Bakthan Singaram, Herbert C. Brown
  • Patent number: 4886924
    Abstract: A process for the stereospecific synthesis of [E] alkenes from enamines comprising the steps of hydroborating the enamine; esterifying the organoborane so formed and oxidizing the boronic ester in the presence of hydrogen peroxide and in the absence of added base under conditions sufficient to form the [E] alkene in high yield.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: December 12, 1989
    Assignee: The Dow Chemical Company
    Inventors: Christian T. Goralski, Bakthan Singaram, Herbert C. Brown
  • Patent number: 4870212
    Abstract: Improved processes for liberating boronic, RB(OR').sub.2, and borinic, RR'BOR', esters from their "ate" complexes, free of alcohol are provided. Pyrolysis of lithium organylborates LiRB(OR').sub.3 and LiRR'BOR', wherein R is an organyl group and R' is straight or branched-chain lower alkyl, directly yields the relatively volatile boronic and borinic esters in high purity, leaving behind a residue of lithium alkoxide. Treatment of the lithium organylborates with an appropriate acid halide cleanly liberates either volatile or non-volatile boronic or borinic esters, readily separated from the lower alkyl ester produced as a by-product. The novel compound lithium dimethylborohydride is also provided.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 26, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4870177
    Abstract: Improved processes for liberating boronic, RB(OR').sub.2, and borinic, RR'BOR', esters from their "ate" complexes, free of alcohol are provided. Pyrolysis of lithium organylborates LiRB(OR').sub.3 and LiRR'BOR', wherein R is an organyl group and R' is straight or branched-chain lower alkyl, directly yields the relatively volatile boronic and borinic esters in high purity, leaving behind a residue of lithium alkoxide. Treatment of the lithium organylborates with an appropriate acid halide cleanly liberates either volatile or non-volatile boronic or borinic esters, readily separated from the lower alkyl ester produced as a by-product. The novel compound lithium dimethylborohydride is also provided.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 26, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4868344
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resoltuion processes ad novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: March 30, 1988
    Date of Patent: September 19, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4868337
    Abstract: A process for synthesizing an optically pure ketone comprising the steps of: treating an appropriate optically pure boronic ester with an organolithium compound at -78.degree. C. to obtain the "ate" complex, separating the optically pure borinic ester from the complex and converting said borinic ester into an optically pure ketone represented by the formulae:R*COR.sup.1 and R*COC.tbd.CR.sup.1wherein R* is a chiral organyl moiety and R.sup.1 is an achiral organyl moeity.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 19, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4866181
    Abstract: A process for preparing optically active alcohols by reducing ketones using mono- or diisopinocampheylhaloboranes as reducing agents.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 12, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4855506
    Abstract: Improved processes for liberating boronic, RB(OR').sub.2' and borinic, RR'BOR', esters from their "ate" complexes, free of alcohol are provided. Pyrolysis of lithium organylborates LiRB(OR').sub.3 and LiRR'BOR', wherein R is an organyl group and R' is straight or branched-chain lower alkyl, directly yields the relatively volatile boronic and borinic esters in high purity, leaving behind a residue of lithium alkoxide. Treatment of the lithium organylborates with an appropriate acid halide cleanly liberates either volatile or non-volatile boronic or borinic esters, readily separated from the lower alkyl ester produced as a by-product. The novel compound lithium dimethylborohydride is also provided.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: August 8, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4795821
    Abstract: A process for synthesizing an optically pure ketone comprising the steps of: treating an appropriate optically pure boronic ester with an organolithium compound at -78.degree. C. to obtain the "ate" complex, separating the optically pure borinic ester from the complex and converting said borinic ester into an optically pure ketone represented by the formulae:R*COR.sup.1 and R*COC.tbd.CR.sup.1wherein R* is a chiral organyl moeity and R.sup.1 is an achiral organyl moeity.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: January 3, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4772752
    Abstract: Novel mono- and diisopinocampheylhaloboranes, represented by the formulae IpcBX.sub.2 and Ipc.sub.2 BX wherein Ipc is isopinocampheyl and X is halo, as well as processes for making and using same.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: September 20, 1988
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4772751
    Abstract: Improved processes for liberating boronic, RB(OR').sub.2, and borinic, RR'BOR', esters from their "ate" complexes, free of alcohol are provided. Pyrolysis of lithium organylborates LiRB(OR').sub.3 and LiRR'BOR', wherein R is an organyl group and R' is straight or branched-chain lower alkyl, directly yields the relatively volatile boronic and borinic esters in high purity, leaving behind a residue of lithium alkoxide. Treatment of the lithium organylborates with an appropriate acid halide cleanly liberates either volatile or non-volatile boronic or borinic esters, readily separated from the lower alkyl ester produced as a by-product. The novel compound lithium dimethylborohydride is also provided.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: September 20, 1988
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4713380
    Abstract: A process for upgrading to essentially 100% enantiomeric excess the optical purity of an organoborane intermediate represented by the formulae:IcpBHR*orIcp.sub.2 BR*wherein Icp is isopinocampheyl and R* is a unsubstituted or substituted, acyclic or cyclic alkyl having from 4 to 30 carbon atoms, comprising the steps of hydroborating cis-alkene, a trans-alkene or a tertiary-alkene with monoisopinocampheylborane or diisopinocampheylborane, obtaining a solid organoborane and recrystallizing the solid organoborane to obtain an enantiomeric excess of essentially 100% ee of said organoborane.
    Type: Grant
    Filed: January 16, 1985
    Date of Patent: December 15, 1987
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown